Winter Park FL Real Estate Guide 2025
Park Avenue Lifestyle • Luxury Homes • Top Schools • Market Trends
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Why Winter Park is Central Florida’s Crown Jewel
- Iconic brick-lined Park Avenue with world-class dining & boutiques
- Chain of Lakes with multimillion-dollar estates & boat tours
- Top-tier public and private schools (Trinity Prep, Lake Highland, Rollins College)
- World-renowned museums: Morse Museum (Tiffany glass), Rollins Museum of Art
- Year-round events: Winter Park Sidewalk Art Festival, Bach Festival, farmers market
- Only 25–30 minutes to MCO airport and theme parks
Winter Park Luxury Estates & Lakefront Homes
The Most Exclusive Addresses in Central Florida
Winter Park is home to some of the most prestigious lakefront estates on the Winter Park Chain of Lakes (Lake Virginia, Lake Osceola, Lake Maitland, and Lake Minnehaha). These properties rarely hit the market and routinely sell from $3M to $18M+.
- Via Tuscany, Via Lugano, Via Capri – “The Vias” – the gold standard
- Olde Winter Park – historic brick-street mansions
- Palmer Avenue & Genius Drive – private gated compounds
- Windsong & Cloister Drive – newer custom estates with boathouses
- Private islands and 2+ acre estates (ultra-rare)
2025 Luxury Market Snapshot:
• Average lakefront sale: $6.8M
• Highest 2025 closing (so far): $17.4M on Lake Maitland
• Days on market for $5M+: 42
• True lakefront inventory: < 12 homes at any time
Lakefront masterpiece on the Winter Park Chain of Lakes
Looking to buy or sell a luxury estate?
The Realtor Stephens Team specializes in $2M+ properties and off-market opportunities.
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Includes lakefront pricing map, school rankings, luxury listings snapshot, buyer/seller checklists, and 2025–2026 forecast
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Frequently Asked Questions
What is the median home price in Winter Park FL in 2025?
As of late 2025, the median sale price ranges from $795,000 – $850,000+ depending on the neighborhood (Olde Winter Park, the Via’s, lakefront estates command $2M–$15M+).
What are the best schools in Winter Park?
Public: Lakemont Elementary, Glenridge Middle, Winter Park High (9/10). Private: Trinity Preparatory, Lake Highland Prep, The Parke House Academy, and Rollins College right in town.
How far is Winter Park from downtown Orlando?
Only 10–15 minutes north via I-4 or Fairbanks Avenue. Orlando International Airport is 25–30 minutes.
Is Winter Park walkable?
Yes! Park Avenue is one of the most walkable downtowns in Florida — boutiques, cafés, museums, and the famous Saturday farmers market all on brick streets under giant oaks.
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